Ammonia → HCID 19261833, compound

HRID 1669131Notes

Reaction equation

HRID 1669131 reaction equation
[N+:1]([C:4]1[C:5]([NH:14]C(=O)C)=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].N>Cl.O>[N+:1]([C:4]1[C:5]([NH2:14])=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 19261343HCID 19261343, compound

Product 1

HCID 19261833HCID 19261833, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of nitroacetamide 167 (151 mg, 0.65 mmol) in 6 M HCl (30 mL) was stirred at 100° C. for 6 h. The suspension was cooled to 20° C., diluted with water (50 mL) and the pH adjusted to 8 with aqueous NH3 solution. The mixture was extracted with DCM (3×50 mL), the combined organic fraction dried, and the solvent evaporated to give amine 174 (113 mg, 100%) as an orange solid: 1H NMR δ 7.83 (s, 1H, H-4), 7.50 (s, 1H, H-1), 5.79 (s, 2H, NH2), 2.67-2.73 (m, 4H, 2×CH2), 1.78-1.83 (m, 4H, 2×CH2).

Workup

  1. temperatureThe suspension was cooled to 20° C.
  2. extractionThe mixture was extracted with DCM (3×50 mL)
  3. customthe combined organic fraction dried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-c41cfb4cefb74c9d898c1bbcf1f3d1bc
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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